N,N'-双(叔丁氧羰基)-L-胱氨酸 | 10389-65-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - BOC-氨基酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N,N'-双(叔丁氧羰基)-L-胱氨酸
• 中文别名: N,N’-双(叔丁氧羰基)-L-胱氨酸
• 英文名称: di-t-butoxycarbonyl-L-cystine
• 英文别名: N,N'-bis(tert-butoxycarbonyl)-L-cystine；N’N’’-bis-Boc-L-cystine；(Boc-Cys-OH)2；(2R)-3-[[(2R)-2-carboxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 10389-65-8
• 化学式: C₁₆H₂₈N₂O₈S₂
• 分子量: 440.539
• InChiKey: MHDQAZHYHAOTKR-UWVGGRQHSA-N

物化性质

• 熔点：
  140-145 °C
• 沸点：
  627.4±55.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸（少量）DMSO（轻微，超声处理），甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  202
• 氢给体数：
  4
• 氢受体数：
  10

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储温度应保持在0-5°C之间。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (Boc-Cys-OH)2
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (Boc-Cys-OH)2
CAS number: 10389-65-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C16H28N2O8S2
Molecular weight: 440.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N,N'–二正丁基氨基甲酸酯-L-半胱氨酸是一种半胱氨酸的衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N,N'-双(叔丁氧羰基)-L-胱氨酸 在 盐酸 、 N,N-二异丙基乙胺 、 锌 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 Boc-S-苄基-L-半光氨酸
  参考文献：
  名称：

  Flemer, Stevenson, Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

  摘要：

  DOI：
• 作为产物：
  描述：

  L-胱氨酸 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以87%的产率得到N,N'-双(叔丁氧羰基)-L-胱氨酸
  参考文献：
  名称：

  叔丁基 2-吡啶碳酸酯。一种用于氨基酸叔丁氧基羰基化的有用试剂

  摘要：

  叔丁基 2-吡啶基碳酸酯是一种稳定的结晶化合物，被发现在氨基酸的叔丁氧基羰基化中非常有效。

  DOI：

  10.1246/cl.1984.237
• 作为试剂：
  描述：

  二氟碘乙酸乙酯 、 在 dipotassium peroxodisulfate 、 iron(II) fluoride 、 N,N'-双(叔丁氧羰基)-L-胱氨酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以76%的产率得到
  参考文献：
  名称：

  一种铁催化芳香族化合物乙氧羰基二氟甲基化的方法

  摘要：

  本发明公开了一种铁催化芳香族化合物乙氧羰基二氟甲基化的方法，该方法包括如下步骤：在溶剂中，以卤二氟乙酸乙酯为氟试剂、过氧化物为氧化剂，铁为催化剂、氨基酸或其衍生物为配体，氧化芳香族化合物的芳香环发生乙氧羰基二氟甲基化反应生成乙氧羰基二氟甲基取代的芳香化合物。本发明方法具有催化剂来源广泛、廉价和环保的优势；氧化剂来源广泛、廉价和不产生废物；氟化试剂温和、稳定和廉价；反应条件温和、选择性高和产率高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；复杂分子和天然产物可兼容，能很好的实现芳香环的乙氧羰基二氟甲基化。在优化的反应条件之下，目标产品分离后产率可以高达90％。

  公开号：

  CN112961054B

文献信息

• Copper‐Promoted O‐Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines
  作者：Adrien Le Roch、Martin Hébert、Alexandre Gagnon

  DOI：10.1002/ejoc.202000790

  日期：2020.9.7

  for the O‐arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is performed in dichloromethane under oxygen at 50 °C in the presence of pyridine, is promoted by copper diacetate, shows excellent scope and functional group tolerance, and retains the integrity of the chiral center. The reactivity of other amino acids possessing a nucleophilic side chain under these

  报道了使用三芳基铋试剂对酪氨酸侧链进行O-芳基化的方法。该反应在吡啶存在下于氧气中于50°C的氧气中于二氯甲烷中进行，由二乙酸铜促进，显示出极好的范围和官能团耐受性，并保留了手性中心的完整性。研究了在这些条件下具有亲核侧链的其他氨基酸的反应性。可以实现含酪氨酸的二肽和三肽的O-酰化。
• Straightforward Functionalization of Sulfur-Containing Peptides via 5- and 6-endo-dig Cyclization Reactions
  作者：Pavel Arsenyan、Sindija Lapcinska

  DOI：10.1055/a-1343-5607

  日期：2021.5

  peptides containing S–S or S–H bonds by employing N-chlorosuccinimide. The corresponding sulfenyl electrophiles are further utilized in 5- and 6-endo-dig cyclization reactions yielding indolizinium salts, indoles, benzo[b]furans, polyaromatic hydrocarbons (PAHs) and isocoumarins, as well as quinolinones bearing a glutathione moiety. PAH derivatives can be used as selective fluorescent dyes for the

  我们提出了一种简单方便的方法，可通过使用N-氯代琥珀酰亚胺从含有S–S或S–H键的肽中生成亚磺基亲电子试剂。相应的亚硫基亲电试剂进一步用于5-和6-内-挖-环化反应，生成吲哚鎓盐，吲哚，苯并[b]呋喃，聚芳烃（PAH）和异香豆素，以及带有谷胱甘肽部分的喹啉酮。PAH衍生物可用作选择性荧光染料，以可视化活细胞中的脂质滴。
• Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders
  申请人：Georgetown University

  公开号：US07202279B1

  公开（公告）日：2007-04-10

  The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

  本发明提供了4-取代-2-氮杂环己酮化合物、双环2-5-二酮哌嗪化合物及其药物组合物，它们是有效、安全且有效的神经保护剂。由于它们具有强大的中枢神经系统（CNS）活性，这些化合物可用于增强记忆力并治疗各种神经系统疾病。这些化合物特别适用于治疗由中枢神经系统创伤引起或与之相关的神经系统疾病。
• Oxidative transformation of thiols to disulfides promoted by activated carbon–air system
  作者：Masahiko Hayashi、Ken-ichi Okunaga、Shunsuke Nishida、Kenjiro Kawamura、Kazuo Eda

  DOI：10.1016/j.tetlet.2010.10.070

  日期：2010.12

  Efficient oxidative transformation of thiols to disulfides took place in the presence of activated carbon under an oxygen (or air) atmosphere. The present oxidation method is available not only for a variety of thiols such as simple aromatic and aliphatic thiols but also for 3,4-dihydropyrimidin-2(1H)-thiones and N-Boc-l-cysteine.

  在氧气（或空气）气氛下，在存在活性炭的情况下，硫醇进行了有效的氧化转化为二硫化物。本氧化方法不仅可用于多种硫醇，例如简单的芳族和脂族硫醇，而且可用于3,4-二氢嘧啶-2（1 H）-硫酮和N- Boc- 1-半胱氨酸。
• New Amino-protective Reagents for<i>t</i>-Butoxycarbonylation and Benzyloxycarbonylation of Amines and Amino Acids
  作者：Sunggak Kim、Jae In Lee、Kyu Yang Yi

  DOI：10.1246/bcsj.58.3570

  日期：1985.12

  New amino-protective reagents for t-butoxycarbonylation and benzyloxycarbonylation of amines and amino acids have been developed. t-Butyl 2-pyridyl carbonate and t-butyl S-(2-pyridyl) thiocarbonate react cleanly with various amines and amino acids to afford N-Boc amines and N-Boc amino acids in high yields. Benzyl 2-pyridyl carbonate and O-benzyl S-(2-pyridyl) thiocarbonate are also found to be very

  已经开发了用于胺和氨基酸的叔丁氧基羰基化和苄氧基羰基化的新型氨基保护试剂。叔丁基 2-吡啶基碳酸酯和叔丁基 S-(2-吡啶基) 硫代碳酸酯与各种胺和氨基酸完全反应，以高产率提供 N-Boc 胺和 N-Boc 氨基酸。也发现苄基 2-吡啶基碳酸酯和 O-苄基 S-(2-吡啶基) 硫代碳酸酯在氨基酸的苄氧羰基化中非常有效。